Deepak Gupta

Land and expand

A small first purchase, then growth through more seats, more usage, or more products in the same account.

Counts as evidence: Net dollar expansion or retention disclosed, or the company names land and expand as its model.

Who ran it

Zoom · Sales routed by deal size, land and expand · 2016 to 2020
Land and expand Primary
Zoom often started in one line of business and spread across departments, which it called land and expand. Its trailing 12-month net dollar expansion rate was 140% at January 2019.
Zoom · Enterprise platform and AI · 2021 to now
Land and expand Supporting
Enterprise net dollar expansion fell from 152% in fiscal 2021 to 98% in fiscal 2026. The 10-K blames slower hiring and seat downsells at existing customers.
HubSpot · Free to Enterprise on one platform · 2018 to 2022
Land and expand Primary
HubSpot described a platform that starts free and grows with the customer, from a team of two to 2,000. By 2021, growth in revenue per customer came mainly from Professional and Enterprise demand.
HubSpot · Beyond search: owned media and answer engines · 2022 to now
Land and expand Primary
Upmarket deals and seat upgrades drive revenue per customer: the CEO said 25% of Pro and Enterprise customers on the seats model had added core seats.
Cursor · Enterprise push and consumption pricing · 2025 to now
Land and expand Supporting
The CEO calls teams the atomic unit Cursor serves. A customer quote on the enterprise page describes adoption growing from 150 to over 500 engineers.
Salesforce · AppExchange and the move to larger customers · 2004 to 2008
Land and expand Primary
Growth inside accounts came from more business units, enterprise-wide deployments and upgrades to fuller editions such as Enterprise Edition. Paying subscriptions went from 147,000 in April 2004 to about 1.1 million in January 2008.
Salesforce · Many clouds, Dreamforce, Trailblazers and acquisitions · 2009 to 2024
Land and expand Primary
More clouds, including acquired products, were sold into the base. The fiscal 2022 10-K frames the Slack deal around the combined enterprise customer bases and the anticipated sales opportunities.
Salesforce · Agentforce, digital labor and consumption pricing · 2024 to now
Land and expand Primary
Benioff says he shipped the product into all 135,000 Salesforce customers. More than 60% of Agentforce and Data 360 bookings in Q4 fiscal 2026 came from existing customer expansion.
Atlassian · Starter licenses, Marketplace and Experts · 2009 to 2019
Land and expand Primary
Land a small team, then grow through seats, renewals, and more products. The fiscal 2009 to 2011 cohorts spent seven times their first purchase over the next five years, helped by an internal Atlassian Engagement Engine that promoted products to users in context.
Atlassian · Free cloud editions and the server sunset · 2019 to 2022
Land and expand Supporting
The cloud migration: no new server licenses from February 2021 and the end of server support in February 2024, with loyalty discounts for large on-premises customers who moved.
Atlassian · Enterprise sales on a cloud-only platform · 2022 to now
Land and expand Primary
Over 90% of FY2026 revenue came from accounts that existed a year earlier, driven by paid seat expansion and price increases. Data Center stopped selling to new customers in March 2026.
Slack · Direct sales layered on self-serve, then Enterprise Grid · 2016 to 2019
Land and expand Primary
Revenue growth came mainly from expansion inside paying customers: Net Dollar Retention of 171%, 152%, and 143% across fiscal 2017 to 2019. Customers paying over $100,000 went from 22% to 40% of revenue, and Enterprise Grid let a company consolidate workspaces into one plan.
Slack · Shared channels, the pandemic, and the sale to Salesforce · 2019 to 2021
Land and expand Supporting
Expansion inside existing customers was still the main revenue driver, but Net Dollar Retention fell from 143% to 132% to 123% between fiscal 2019 and 2021.
Slack · Sold by Salesforce, free tier tightened, repositioned for AI agents · 2021 to now
Land and expand Supporting
Salesforce describes Slack as integrated with every Salesforce offering, including Agentforce, and as the conversational interface where people and agents work together, with a built-in Slackbot agent.
Figma · FigJam, Dev Mode, Enterprise and the Adobe deal · 2021 to 2023
Land and expand Primary
FigJam (2021) took Figma into brainstorming for extended teams, free through 2021 with paid plans in 2022. Dev Mode (2023) gave developers their own paid workspace, free in beta for 2023 and paid from 2024. Net dollar retention expanded through 2024 after Dev Mode.
Figma · Platform seats, IPO and AI credits · 2024 to now
Land and expand Primary
About 70% of new Organization and Enterprise customers already had a Professional plan member, and 76% of customers used two or more products. In March 2025 Figma ended user-driven upgrades: any seat upgrade now needs administrator approval, and Full seat prices rose 20% to 33%.
Twilio · Inverting the enterprise sales model · 2015 to 2018
Land and expand Primary
Revenue grew as customers' apps scaled, found new uses, or added products. Dollar-Based Net Expansion Rate was 155% in 2015 and 161% in 2016, then 128% in 2017 after Uber, the largest Base Customer, reduced its usage.
Twilio · Platform by acquisition and the enterprise push · 2019 to 2021
Land and expand Primary
Expansion shifted from more usage of one API to more products per account: email through SendGrid and customer data through Segment, the latter valued at about $3.2 billion in stock. Net expansion stayed at 135% to 137%.
Twilio · Slowdown, split, and refocus · 2022 to 2023
Land and expand Supporting
Expansion slowed: Dollar-Based Net Expansion Rate fell from 137% in 2020 to 131% in 2021 and 121% in 2022.
Twilio · Three motions, ISVs, and AI · 2024 to now
Land and expand Supporting
Cross-selling is an explicit priority. Net expansion went from 103% in 2023 to 108% in 2025 and 116% in the second quarter of 2026.
Datadog · Inside sales, enterprise team, and multi-product expansion · 2016 to 2019
Land and expand Primary
Customers land on one product and expand on a self-service basis. Net retention was 141% to 151%, and about 60% of new customers in the first half of 2019 landed with more than one product, up from about 15% a year earlier.
Datadog · Platform expansion and peak net retention · 2020 to 2022
Land and expand Primary
Cloud SIEM, Incident Management, Cloud Security Posture Management, and Database Monitoring were among the 2020 and 2021 launches. About 81% of customers used more than one product at December 2022, and trailing net retention for that month was later restated as mid-140s.
Datadog · Usage optimization, enterprise scale, and AI · 2023 to now
Land and expand Primary
At December 2025, about 55% of customers used four or more products, 18% eight or more, and 9% ten or more. Launches in 2024 and 2025 included LLM Observability, OnCall, Product Analytics, and Bits AI SRE.
Snowflake · Land and expand, the IPO, and the Data Cloud · 2019 to 2021
Land and expand Primary
About 94% of revenue in the six months to July 31, 2020 came from existing capacity customers. Net revenue retention was 169% for fiscal 2020 and 158% at July 31, 2020.
Snowflake · Scaling through clouds, partners, and developers · 2021 to 2024
Land and expand Primary
Net revenue retention went from 178% in fiscal 2022 to 158% in fiscal 2023 and 131% in fiscal 2024, per the FY2024 10-K, as customers cut storage and optimized consumption.
Snowflake · The AI Data Cloud and agents · 2023 to now
Land and expand Primary
The CFO calls landing and expanding customers the two fundamentals. Net revenue retention was 133%, 126%, and 125% for fiscal 2024 to 2026 in the FY2026 10-K's restated series, while 740 net new customers in the quarter was up 40%.
CrowdStrike · Modules, trial-to-pay, marketplace and channel · 2017 to 2020
Land and expand Primary
Customers start with any number of modules, and more are activated in real time on the agent already deployed. Net retention was 104%, 119% and 147% at January 2017, 2018 and 2019, and 47% of customers had four or more modules by January 2019.
CrowdStrike · Platform scale and module depth · 2020 to 2024
Land and expand Primary
Customers with five or more modules went from 33% at January 2020 to 57% at January 2022 and 64% at January 2024, the last excluding Falcon Go bundles. Falcon Flex replaced fixed bundles with a model where customers expand, adopt and swap modules without new procurement cycles.
CrowdStrike · After the July 2024 incident: Flex and partner-first · 2024 to now
Land and expand Primary
The 10-K says customer commitment packages included discounting, additional modules, professional services, flexible payment terms or subscription extensions, and have increased contraction and decreased upsell dollar values. Guidance in August 2024 included an estimated $30M subscription revenue impact in each remaining FY2025 quarter from those incentives. ARR from Falcon Flex accounts reached $1.69B at January 2026 and over $2.29B at July 2026.
Okta · Platform, land and expand, and the IPO · 2014 to 2017
Land and expand Primary
After the first sale, Okta adds users and sells more products, often within the term of the first contract. Large enterprises often start with a limited deployment before going broader.
Okta · Public scale-up of the workforce engine · 2017 to 2021
Land and expand Primary
The FY2018 10-K says dollar-based retention consistently exceeded 120%, driven by more users and up-selling products. It was 121%, 119% and 120% in the trailing periods reported in the FY2021 10-K.
Okta · Auth0, two clouds, and security incidents · 2021 to 2024
Land and expand Primary
Expansion now includes moving from workforce identity into customer identity. Dollar-based net retention peaked at 124% in FY2022.
Okta · Specialized sales, profitability and AI agents · 2024 to now
Land and expand Primary
Cross-sell runs from workforce to customer identity or the reverse, and new products led by Okta Identity Governance add growth. Net retention fell to 106% in FY2026, and the 10-K warns that customer workforce cuts can reduce revenue.
Anthropic · Claude Code and the enterprise build-out · 2025 to 2025
Land and expand Supporting
Accounts with over $100,000 in run-rate revenue grew nearly 7x in the year to September 2025. A customer quoted by Anthropic says bundling Claude for Enterprise with Claude Code led to a rollout to hundreds of developers.
Anthropic · Partner network, three clouds, expansion · 2026 to now
Land and expand Primary
Anthropic says businesses that start with Claude for a single use case expand their integrations across the organisation. Customers spending over $1 million a year went from a dozen to over 500 in two years.
Replit · Community platform and paid power · 2021 to 2023
Land and expand Tried, then dropped
Teams Pro, launched January 2022, sold Replit for work as a shared team space for company code. It was later replaced by the 2024 Teams product. No source gives its results.
Replit · Enterprise through the product, marketplaces, and partners · 2025 to now
Land and expand Supporting
Enterprise plans are annual commitments turned into credits with unlimited seats, pooled across the organisation. The CEO says enterprise churn is very low and net retention reaches 300% in some cases.
Dropbox · Team plans on top of individual adoption · 2011 to 2015
Land and expand Primary
Teams added admin controls, central billing, and phone support, priced at $795 a year for five users plus $125 per extra seat. The Golden State Warriors started with 15 licenses in 2013 and later requested 450.
Dropbox · Focus on work, self-serve at scale, IPO · 2015 to 2019
Land and expand Primary
Individual subscribers who collaborate are prompted to buy team plans. In 2017 over 40% of new Dropbox Business teams included a former individual subscriber.
Dropbox · Multi-product, restructuring, and AI · 2020 to now
Land and expand Supporting
Dash, an AI-powered universal search tool, is offered to teams at an additional cost, a second product sold to the same buyer.
Notion · B2C2B: personal users carry Notion into teams · 2021 to 2024
Land and expand Primary
The CEO calls the internal strategy B2C2B: people bring Notion to work, and half of B2B customers came from prior personal users. In December 2022 Notion added a Business tier between Plus and Enterprise, and in February 2023 Notion AI, which had drawn more than 2 million waitlist signups, became a $10 per member add-on on any plan.
Notion · AI in the business plans, enterprise sales, agent credits · 2025 to now
Land and expand Primary
In May 2025 the Business and Enterprise plans began including unlimited Notion AI, with enterprise search, research mode, and meeting notes, at new prices. Notion says more than 50% of ARR came from AI-enabled customers at the end of 2025, a share that more than doubled in a year.
Stripe · Startups first, beyond payments · 2016 to 2019
Land and expand Primary
New products were built on the payments base and sold to existing users. Billing was an evolution of Subscriptions built from customer feedback, Radar launched in 2016, and Atlas put founders on Stripe at incorporation.
Stripe · March into the enterprise · 2020 to 2022
Land and expand Supporting
Enterprise deals could start beyond core payments. Atlassian moved its subscription and revenue management onto Stripe Billing, with over a dozen custom features designed with Stripe.
Stripe · Multi-product platform for startups and enterprises · 2023 to now
Land and expand Primary
Billing grew into a Revenue and Finance Automation suite (Billing, Tax, Revenue Recognition, and later Metronome usage billing) sold into the payments base. It passed a $500 million run rate and is on track for $1 billion.
Shopify · Payments, paid search and the IPO · 2013 to 2015
Land and expand Supporting
Merchants who grew moved to higher plans and used more merchant solutions, and the F-1 says higher billings from remaining merchants largely offset decline within each cohort.
Shopify · Shopify Plus, Unite and merchant solutions take over · 2016 to 2019
Land and expand Primary
Merchants start on cheap plans and grow into higher ones. Over half of the first 1,000+ Plus merchants were upgrades, and most GMV came from the Advanced and Plus plans, where retention is also higher.
Gong · Platform across the revenue organisation · 2023 to 2024
Land and expand Primary
Gong described companies consolidating on its platform, and reported that across 332 customers, those using Gong throughout the organization saw 11% higher revenue growth year over year. Market intelligence was already drawing product and marketing teams by 2020.
Gong · Revenue AI OS, enterprise expansion, marketplace · 2025 to now
Land and expand Primary
Multi-product use rose from one in four customers in March 2025 to half in May 2026, use spread to RevOps, enablement, success, support, and services, and Gong added more $1M+ customers in two quarters than in the previous six.
Canva · Canva for Work and 100 languages · 2015 to 2019
Land and expand Supporting
The paid plan was aimed at organisations already on the free product: more than 200,000 companies, some with up to 180 employees on Canva, and more than 40% of the Fortune 500.
Canva · Teams, classrooms and the workplace · 2020 to 2023
Land and expand Primary
Team adoption more than quadrupled in the twelve months to September 2021, helped by a limited pay-for-one, get-four-free Pro offer. In 2022 Canva Teams became the plan for two or more people, with brand controls once limited to Enterprise, and by December 2023 there were 135,000 teams in companies of more than 1,000 employees.
Canva · Enterprise rebuilt, pro tools and AI distribution · 2024 to now
Land and expand Primary
The ladder now runs Free, Pro, Business from October 2025, and Enterprise, which moves users into organisation-managed workspaces. A 2024 Teams price change to US$10 a month per person from three people was eased for early adopters after pushback.
MongoDB · Enterprise Advanced and direct sales · 2013 to 2016
Land and expand Primary
A first application lands, then more applications, departments, and geographies follow. Net ARR expansion was 128% at July 2017 and above 120% for ten straight quarters before the IPO.
MongoDB · Atlas becomes the business, sold with the clouds · 2019 to now
Land and expand Primary
Land a workload, find adjacencies, then become the company standard. Net ARR expansion was about 121% at January 31, 2026.
GitLab · Open core and buyer-based tiers · 2015 to 2019
Land and expand Supporting
Large accounts began to appear: a first $100,000 ARR customer in 2017, the Ultimate tier at $99 per month in 2018, 20 such customers that year, and a first $1 million ARR customer in 2019.
GitLab · Enterprise sales, partners, and the IPO · 2019 to 2021
Land and expand Primary
The customer journey begins with developers and expands to senior executive buyers, with organizations moving into higher tiers such as Ultimate for security. Dollar-based net retention was 179% in FY2020 and 148% in FY2021.
GitLab · Pruning the cheap tier and the free ceiling · 2021 to 2024
Land and expand Primary
Starter and Bronze, 27% of FY2020 revenue, were ended for missing the company's hurdle rate, with customers moved to Free or Premium. Premium then rose from $19 to $29 per user per month, GitLab's first price increase in more than five years.
GitLab · AI agents and hybrid pricing · 2024 to now
Land and expand Supporting
Expansion is now sold as users, tiers, and credits, while dollar-based net retention fell from 130% in FY2024 to 118% in FY2026 and 117% in the quarter to July 2026.
Asana · Self-serve first, sales to expand · 2017 to 2023
Land and expand Primary
Customers typically landed with one use case in one department and expanded to others. Dollar-based net retention was over 120% overall at January 2022, over 130% for customers spending over $5,000, and over 145% for those spending over $50,000.
Asana · Up-market and top-down sales · 2023 to 2025
Land and expand Supporting
Expansion slowed sharply: overall dollar-based net retention went from over 115% at January 2023 to over 100% at January 2024 and 96% at January 2025.
Asana · AI Studio, credits, and the agentic platform · 2024 to now
Land and expand Supporting
Dollar-based net retention was 96% at January 2026 and 97% overall in Q2 FY2027, improving in every reported cohort. Rogers says customers using AI Studio and AI Teammates retain better and expand faster.
Cloudflare · Enterprise sales layered on self-serve · 2016 to 2019
Land and expand Primary
Customers start with part of their network needs and add products with one click. Over 70% of enterprise customers used four or more products, and net retention stayed above 110% for eight quarters.
Cloudflare · Developer platform on the network · 2017 to 2024
Land and expand Primary
Dollar-based net retention rose to 125% at the end of 2021, then eased to 115% at the end of 2023.
Cloudflare · Contracted customers, channel and agents · 2025 to now
Land and expand Supporting
Dollar-based net retention reaccelerated to 120% at the end of 2025, from 111% a year earlier.
monday.com · Sales, partners and the Work OS · 2018 to 2021
Land and expand Primary
Large accounts start with a small team and spread. Customers over $50,000 ARR went from 76 to 264 in 2020, net dollar retention for customers with more than 10 users reached 121%, and the 2016 and 2017 cohorts expanded faster once sales and customer success worked them.
monday.com · More products and the move upmarket · 2021 to 2024
Land and expand Primary
Work management, sales CRM, dev and later service were sold on one platform. Customers over $50,000 ARR reached 3,201 at the end of 2024. Net dollar retention for customers with more than 10 users was over 135% at the end of 2021 and 115% at the end of 2023, which the company tied to slower expansion.
monday.com · Hybrid sales-led GTM and the AI Work Platform · 2025 to now
Land and expand Primary
Expansion runs through seat penetration, more products and AI adoption. Customers over $500,000 ARR rose from 50 to 87 in 2025, and net dollar retention for customers over $50,000 ARR was 116%.
Zscaler · Second product, land and expand, IPO · 2016 to 2020
Land and expand Primary
Customers start with some users, then add users, upgrade to richer suites, and cross-buy ZIA or ZPA. Dollar-based net retention ran from 115% to 120% across fiscal 2017 to 2020.
Zscaler · The Zero Trust Exchange reframing · 2020 to 2023
Land and expand Primary
Zscaler Digital Experience (ZDX) joined ZIA and ZPA, and dollar-based net retention rose to 128% in fiscal 2021 before easing to 121% in fiscal 2023.
Zscaler · Platform, flexible spend, and AI security · 2023 to now
Land and expand Primary
Expansion now runs through more products, non-seat pricing, and Z-Flex, a pre-committed spend pool customers draw on for new products. Net retention was 114% in fiscal 2025, and the FY2026 10-K reports ARR of $3,771M instead of a net retention rate.
Lovable · Credits, giveaways, and a community at scale · 2025 to 2026
Land and expand Supporting
Net dollar retention comes from builders buying more credits to build. Workspaces have unlimited members drawing on one shared credit pool, so inviting people does not change the subscription cost.
Lovable · Enterprise, partners, and marketplaces · 2025 to now
Land and expand Primary
Adoption starts with employees building internal tools, prototypes, and landing pages, then spreads. Lovable says it reached employees at half of the Fortune 500 in its first year and nearly two-thirds less than a year later, and names a customer that rolled it out to 200+ employees.
OpenAI · Self-serve teams, ecosystem, and campus · 2024 to 2025
Land and expand Supporting
By November 2025 OpenAI reported more than 7 million ChatGPT for Work seats, up 40% in two months, with Enterprise seats up 9x year over year. ChatGPT Edu was built from university Enterprise deployments.